JOHN CUSACK

Despite the roles he has been in, those of sentimental suitors, like Lloyd Dobler and Rob Gordon in Say Anything and High Fidelity, respectively—John Cusack has never been blessed (or cursed, depending on how you see it) with a fairy tale marriage. Despite having dated quite many high-profile Hollywood women, Cusack, to some degree, has not given marriage any thought.

In fact, for an interview with Elle Magazine, he was asked to describe in five words why he never got married, and the actor wittily responded that he could do it in seven and that is society doesn’t tell him what to do. Despite not getting married, he had a history where he dated women, including Baywatch star Brooke Burns and Jennifer Love Hewitt, and was seen together on the movie premiere of Identity last 2003. Although he is not lucky enough to have a permanent life partner, his career as a celebrity still shines through.